Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes

被引：139

作者：

Gevorgyan, V ^{[1
]}

Quan, LG ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai 9808578, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(99)00656-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

o-Bromobenzaldehyde 1, in the presence of a palladium catalyst, smoothly underwent consecutive intermolecular carbopalladation with internal alkynes 2 and then intramolecular nucleophilic vinylpalladation of the aldehyde function to produce the indenol derivatives 4 in high yields. Further heating of 4 under more elevated temperature caused complete isomerization to the corresponding indanones 8. A mechanism for this nucleophilic vinylpalladation of aromatic aldehydes is proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4089 / 4092

页数：4

共 7 条

[1] REDUCTION OF ACID-CHLORIDES WITH SODIUM-BOROHYDRIDE IN N,N-DIMETHYLFORMAMIDE - NATURE OF THE REACTION INTERMEDIATE AND A METHOD FOR ITS CONVERSION TO THE CORRESPONDING ALDEHYDE WITH MINIMAL ALCOHOL FORMATION [J].

BABLER, JH ;

INVERGO, BJ .

TETRAHEDRON LETTERS, 1981, 22 (01) :11-14

[2] CATALYTIC TRANSFER HYDROGENATION [J].

BRIEGER, G ;

NESTRICK, TJ .

CHEMICAL REVIEWS, 1974, 74 (05) :567-580

[3] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].

CABRI, W ;

CANDIANI, I .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7

[4] SYNTHESIS OF INDENONES VIA PALLADIUM-CATALYZED ANNULATION OF INTERNAL ALKYNES [J].

LAROCK, RC ;

DOTY, MJ ;

CACCHI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4579-4583

[5] Cyclic carbopalladation. A versatile synthetic methodology for the construction of cyclic organic compounds [J].

Negishi, EI ;

Coperet, C ;

Ma, SM ;

Liou, SY ;

Liu, F .

CHEMICAL REVIEWS, 1996, 96 (01) :365-393

[6] Transition metal-catalyzed carbocyclizations in organic synthesis [J].

Ojima, I ;

Tzamarioudaki, M ;

Li, ZY ;

Donovan, RJ .

CHEMICAL REVIEWS, 1996, 96 (02) :635-662

[7]

QUAN LG, 1999, IN PRESS J AM CHEM S, V121

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